Sodium Hydroxide → HCID 19430567, compound

HRID 1077981Notes

Reaction equation

HRID 1077981 reaction equation
[F:1][C:2]([F:54])([F:53])[C:3]1[CH:4]=[C:5]([S:13]([N:16]([C:34]2[CH:50]=[C:49]([Cl:51])[C:48]([Cl:52])=[CH:47][C:35]=2[O:36][C:37]2[CH:46]=[CH:45][CH:44]=[CH:43][C:38]=2[C:39]([O:41]C)=[O:40])S(C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)(=O)=O)(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Na+]>CO>[F:54][C:2]([F:1])([F:53])[C:3]1[CH:4]=[C:5]([S:13]([NH:16][C:34]2[CH:50]=[C:49]([Cl:51])[C:48]([Cl:52])=[CH:47][C:35]=2[O:36][C:37]2[CH:46]=[CH:45][CH:44]=[CH:43][C:38]=2[C:39]([OH:41])=[O:40])(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19430568HCID 19430568, compound

Product 1

HCID 19430567HCID 19430567, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-[2-[N,N-bis-[3-,5-bis(trifluoromethyl)phenylsulfonyl]amino]-4,5-dichlorophenoxy]benzoate (0.4 g, 0.46 mmol) was dissolved in methanol (5 mL), a 1N solution of sodium hydroxide (3 mL, 3 mmol) was added and the mixture was stirred for 16 h at room temperature. The solvents were evaporated and the residue was acidified with dilute HCl, extracted with EtOAc, dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid), and then recrystallized from EtOAc/hexane to give the title compound; mp 139°-140° C.

Workup

  1. customThe solvents were evaporated
  2. extractionextracted with EtOAc
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid)
  7. customrecrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-ca99f15270044151bc7ff89c4c204e5f
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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